ES2243585T3 - Procedimiento para la acilacion en cintinuo de derivados del ester de cromanol. - Google Patents

Procedimiento para la acilacion en cintinuo de derivados del ester de cromanol.

Info

Publication number: ES2243585T3
Authority: ES; Spain
Prior art keywords: column; reaction; formula; tocopherol; reactor
Prior art date: 2000-11-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES01989492T

Other languages

English (en)

Spanish (es)

Inventor

Carsten Oost

Gerd Kaibel

Harald Laas

Peter Schmitt

Jens Von Erden

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-11-22

Filing date

2001-11-21

Publication date

2005-12-01

2001-11-21 Application filed by BASF SE filed Critical BASF SE

2005-12-01 Application granted granted Critical

2005-12-01 Publication of ES2243585T3 publication Critical patent/ES2243585T3/es

2021-11-21 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 57
-1 chromanol ester Chemical class 0.000 claims abstract description 33
230000010933 acylation Effects 0.000 claims abstract description 23
238000005917 acylation reaction Methods 0.000 claims abstract description 23
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 21
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 15
238000006243 chemical reaction Methods 0.000 claims description 111
SEBPXHSZHLFWRL-UHFFFAOYSA-N 3,4-dihydro-2,2,5,7,8-pentamethyl-2h-1-benzopyran-6-ol Chemical class O1C(C)(C)CCC2=C1C(C)=C(C)C(O)=C2C SEBPXHSZHLFWRL-UHFFFAOYSA-N 0.000 claims description 29
239000003153 chemical reaction reagent Substances 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 26
239000003054 catalyst Substances 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 17
238000009835 boiling Methods 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
150000008065 acid anhydrides Chemical class 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000007795 chemical reaction product Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
238000012856 packing Methods 0.000 claims description 6
238000011144 upstream manufacturing Methods 0.000 claims description 5
239000000945 filler Substances 0.000 claims description 4
238000010926 purge Methods 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 2
239000003292 glue Substances 0.000 claims description 2
239000011732 tocopherol Substances 0.000 abstract description 34
229930003799 tocopherol Natural products 0.000 abstract description 32
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239000011731 tocotrienol Substances 0.000 abstract description 14
235000019148 tocotrienols Nutrition 0.000 abstract description 14
GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 abstract description 11
235000019149 tocopherols Nutrition 0.000 abstract description 11
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150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
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GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 85
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 70
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
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150000008064 anhydrides Chemical class 0.000 description 14
238000005194 fractionation Methods 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
238000000926 separation method Methods 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 10
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000004821 distillation Methods 0.000 description 8
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
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238000010992 reflux Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
238000009434 installation Methods 0.000 description 6
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239000011709 vitamin E Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
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ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 5
238000004064 recycling Methods 0.000 description 5
150000003611 tocopherol derivatives Chemical class 0.000 description 5
239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 description 4
150000001242 acetic acid derivatives Chemical class 0.000 description 4
230000021736 acetylation Effects 0.000 description 4
238000006640 acetylation reaction Methods 0.000 description 4
BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 description 4
238000006555 catalytic reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000002815 homogeneous catalyst Substances 0.000 description 4
BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 description 4
235000005074 zinc chloride Nutrition 0.000 description 4
239000011592 zinc chloride Substances 0.000 description 4
GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
WVQUCYVTZWVNLV-UHFFFAOYSA-N boric acid;oxalic acid Chemical compound OB(O)O.OC(=O)C(O)=O WVQUCYVTZWVNLV-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
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229910052751 metal Inorganic materials 0.000 description 3
OTXNTMVVOOBZCV-UHFFFAOYSA-N 2R-gamma-tocotrienol Natural products OC1=C(C)C(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-UHFFFAOYSA-N 0.000 description 2
241000282414 Homo sapiens Species 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
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238000001704 evaporation Methods 0.000 description 2
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238000004508 fractional distillation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000002638 heterogeneous catalyst Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000463 material Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
229910052682 stishovite Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000032258 transport Effects 0.000 description 2
229910052905 tridymite Inorganic materials 0.000 description 2
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WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 2
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
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230000001932 seasonal effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003712 vitamin E derivatives Chemical class 0.000 description 1
238000005303 weighing Methods 0.000 description 1
RZFHLOLGZPDCHJ-XZXLULOTSA-N α-Tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C RZFHLOLGZPDCHJ-XZXLULOTSA-N 0.000 description 1
235000019145 α-tocotrienol Nutrition 0.000 description 1
239000011730 α-tocotrienol Substances 0.000 description 1
235000007680 β-tocopherol Nutrition 0.000 description 1
239000011590 β-tocopherol Substances 0.000 description 1
235000019151 β-tocotrienol Nutrition 0.000 description 1
239000011723 β-tocotrienol Substances 0.000 description 1
FGYKUFVNYVMTAM-WAZJVIJMSA-N β-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-WAZJVIJMSA-N 0.000 description 1
239000002478 γ-tocopherol Substances 0.000 description 1
QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
235000019150 γ-tocotrienol Nutrition 0.000 description 1
239000011722 γ-tocotrienol Substances 0.000 description 1
OTXNTMVVOOBZCV-WAZJVIJMSA-N γ-tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-WAZJVIJMSA-N 0.000 description 1
239000002446 δ-tocopherol Substances 0.000 description 1
235000019144 δ-tocotrienol Nutrition 0.000 description 1
239000011729 δ-tocotrienol Substances 0.000 description 1
ODADKLYLWWCHNB-LDYBVBFYSA-N δ-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 ODADKLYLWWCHNB-LDYBVBFYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
- B01D3/146—Multiple effect distillation
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/32—Other features of fractionating columns ; Constructional details of fractionating columns not provided for in groups B01D3/16 - B01D3/30
- B01D3/322—Reboiler specifications
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D1/00—Evaporating
- B01D1/22—Evaporating by bringing a thin layer of the liquid into contact with a heated surface
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Pyrane Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

ES01989492T 2000-11-22 2001-11-21 Procedimiento para la acilacion en cintinuo de derivados del ester de cromanol. Expired - Lifetime ES2243585T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10058132		2000-11-22
DE10058132		2000-11-22

Publications (1)

Publication Number	Publication Date
ES2243585T3 true ES2243585T3 (es)	2005-12-01

Family

ID=7664369

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES01989492T Expired - Lifetime ES2243585T3 (es)	2000-11-22	2001-11-21	Procedimiento para la acilacion en cintinuo de derivados del ester de cromanol.

Country Status (8)

Country	Link
US (1)	US6784303B2 (de)
EP (1)	EP1339704B1 (de)
CN (1)	CN1205200C (de)
AT (1)	ATE298330T1 (de)
AU (1)	AU2002227934A1 (de)
DE (1)	DE50106594D1 (de)
ES (1)	ES2243585T3 (de)
WO (1)	WO2002042286A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2004096790A1 (en) *	2003-04-28	2004-11-11	Dsm Ip Assets B.V.	Process for the manufacture of tocyl and tocopheryl acylates
EP1622887B1 (de) *	2003-05-02	2010-07-28	DSM IP Assets B.V.	Verfahren zur herstellung von tocyl- und tocopheryl-acylaten
DE102004012904A1 (de) *	2004-03-17	2005-10-06	Bayer Chemicals Ag	Verfahren zur kontinuierlichen Zerlegung von Stoffgemischen
EP1740567B1 (de) *	2004-04-26	2007-08-22	DSMIP Assets B.V.	Verfahren zur herstellung von tocopherylacylaten
KR101140519B1 (ko) *	2004-06-11	2012-04-30	디에스엠 아이피 어셋츠 비.브이.	크로만 유도체, 특히 α-토코페롤 및 그의 알카노에이트의제조 방법
ATE502931T1 (de)	2004-08-19	2011-04-15	Dsm Ip Assets Bv	Verfahren zur rektifikation von vitamin e acetat
WO2006018310A2 (en)	2004-08-19	2006-02-23	Dsm Ip Assets B.V.	Process for the working-up of a vitamin e- and vitamin e-acetate and rectification colum suitable therefore
CN106565659B (zh) *	2016-11-01	2019-06-18	万华化学集团股份有限公司	一种制备维生素e乙酸酯的方法

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US3444213A (en)	1967-07-12	1969-05-13	Eastman Kodak Co	Continuous process for producing dl alpha tocopherol
US3708505A (en)	1971-02-25	1973-01-02	Diamond Shamrock Corp	Process for preparation of d,l-alpha tocopherol
JPS4955633A (de) *	1972-10-12	1974-05-30
CS205951B1 (cs) *	1978-10-25	1981-05-29	Miloslav Gablech	Způsob kontinuální výroby d,l-alfa-tokoferolacetátu
DE4208477A1 (de)	1992-03-17	1993-09-23	Basf Ag	Verfahren zur herstellung von vitamin e
US5886196A (en)	1996-01-12	1999-03-23	Roche Vitamins Inc.	Method of catalyzing condensation reactions
JP2002502360A (ja) *	1996-01-29	2002-01-22	ビーエーエスエフアクチェンゲゼルシャフト	ｄｌα―トコフェロールまたは酢酸ｄｌ―α―トコフェリルの製造方法
DE19603142A1 (de)	1996-01-29	1997-07-31	Basf Ag	Verfahren zur Herstellung von dl-alpha-Tocopherol oder dl-alpha-Tocopherylacetat
US6005122A (en) *	1996-12-23	1999-12-21	Basf Aktiengesellschaft	Preparation of α-tocopherol or α-tocopheryl acetate by reacting trimethylhydroquinone and phytol or isophytol, with recycling of the zinc halide condensation catalyst
DE19704619A1 (de) *	1997-02-07	1998-08-13	Basf Ag	Verfahren zur Herstellung von Tocopherylcarbonsäureestern oder Tocotrienylestern durch säurekatalysierte Umsetzung mit Carbonsäuren

2001
- 2001-11-21 AT AT01989492T patent/ATE298330T1/de not_active IP Right Cessation
- 2001-11-21 ES ES01989492T patent/ES2243585T3/es not_active Expired - Lifetime
- 2001-11-21 US US10/416,468 patent/US6784303B2/en not_active Expired - Fee Related
- 2001-11-21 AU AU2002227934A patent/AU2002227934A1/en not_active Abandoned
- 2001-11-21 EP EP01989492A patent/EP1339704B1/de not_active Expired - Lifetime
- 2001-11-21 CN CNB018193501A patent/CN1205200C/zh not_active Expired - Lifetime
- 2001-11-21 WO PCT/EP2001/013472 patent/WO2002042286A1/de not_active Ceased
- 2001-11-21 DE DE50106594T patent/DE50106594D1/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US20040014996A1 (en)	2004-01-22
WO2002042286A1 (de)	2002-05-30
AU2002227934A1 (en)	2002-06-03
CN1476441A (zh)	2004-02-18
CN1205200C (zh)	2005-06-08
ATE298330T1 (de)	2005-07-15
EP1339704B1 (de)	2005-06-22
EP1339704A1 (de)	2003-09-03
US6784303B2 (en)	2004-08-31
DE50106594D1 (de)	2005-07-28

Publication	Publication Date	Title
BR0014732B1 (pt)	2011-07-12	método de produção de acetato de etila.
AR070948A1 (es)	2010-05-19	Metodo y aparato para preparar acido acetico con purificacion mejorada
BR9909040B1 (pt)	2010-11-16	processo e aparelho para a produção de acetato de butila e acetato de isobutila.
KR20000057502A (ko)	2000-09-15	비닐 아세테이트의 제조방법
ES2205470T3 (es)	2004-05-01	Procedimiento para la separacion de agua.
US8592624B2 (en)	2013-11-26	Production of ethylenically unsaturated acids or esters thereof
EP0150962B1 (de)	1989-08-30	Transesterifizierungsverfahren
CN105324164A (zh)	2016-02-10	用于提纯含有α-羟基羧酸的环酯的料流的方法与设备
CA1083600A (en)	1980-08-12	Continuous production of 2-ethyl-hexyl acrylate free from dioctylether
KR20130051453A (ko)	2013-05-20	추출 증류에 의한 카르복실산 에스테르의 정제
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US6784303B2 (en)	2004-08-31	Method for continuously acylating chromanol ester derivatives
JPH07507274A (ja)	1995-08-10	ビタミンｅの製法
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US4329484A (en)	1982-05-11	Continuous process for preparing acyloxysilanes
JPS6023345A (ja)	1985-02-05	グリオキシル酸エステルの製法
JPS6232180B2 (de)	1987-07-13
EP0108540B1 (de)	1986-07-09	Herstellung von Phenylestern in Gegenwart von Borsäureanhydrid
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US4215055A (en)	1980-07-29	Production of liquid ortho-phthalic acid and its conversion to high _purity phthalic anhdyride
US4845247A (en)	1989-07-04	3,4,-dihydro-2H-pyrans
CN112888678B (zh)	2025-03-07	色原烷醇和2-甲基-1,4-萘醌衍生物的合成
FI90656B (fi)	1993-11-30	Menetelmä 2-(4-isobutyylifenyyli)-propionihapon puhdistamiseksi
JP2002363132A (ja)	2002-12-18	２，２，４−トリメチル−１，３−ペンタンジオールジイソブチレートの製造方法